SK3032003A3 - Method for producing peptide salts, their use and pharmaceutical preparations containing these peptide salts - Google Patents
Method for producing peptide salts, their use and pharmaceutical preparations containing these peptide salts Download PDFInfo
- Publication number
- SK3032003A3 SK3032003A3 SK303-2003A SK3032003A SK3032003A3 SK 3032003 A3 SK3032003 A3 SK 3032003A3 SK 3032003 A SK3032003 A SK 3032003A SK 3032003 A3 SK3032003 A3 SK 3032003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- peptide
- salt
- acid
- cetrorelix
- diluent
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 42
- 150000003839 salts Chemical class 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 239000000825 pharmaceutical preparation Substances 0.000 title abstract 3
- 241000124008 Mammalia Species 0.000 claims abstract 2
- 238000007911 parenteral administration Methods 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 108700008462 cetrorelix Proteins 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 229960003230 cetrorelix Drugs 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 6
- -1 Azalin B Chemical compound 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 238000004108 freeze drying Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- NOENHWMKHNSHGX-IZOOSHNJSA-N (2s)-1-[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-(ca Chemical compound C([C@H](C(=O)N[C@H](CCCCNC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 NOENHWMKHNSHGX-IZOOSHNJSA-N 0.000 claims description 3
- WDYSQADGBBEGRQ-APSDYLPASA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-[(2r,3r,4r,5r,6s) Chemical compound C([C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O WDYSQADGBBEGRQ-APSDYLPASA-N 0.000 claims description 3
- 108010023617 abarelix Proteins 0.000 claims description 3
- AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 claims description 3
- 229960002184 abarelix Drugs 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 108010070670 antarelix Proteins 0.000 claims description 3
- 108700027435 detirelix Proteins 0.000 claims description 3
- 108700032141 ganirelix Proteins 0.000 claims description 3
- GJNXBNATEDXMAK-PFLSVRRQSA-N ganirelix Chemical compound C([C@@H](C(=O)N[C@H](CCCCN=C(NCC)NCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 GJNXBNATEDXMAK-PFLSVRRQSA-N 0.000 claims description 3
- 229960003794 ganirelix Drugs 0.000 claims description 3
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 108010092834 ramorelix Proteins 0.000 claims description 3
- 229950000277 ramorelix Drugs 0.000 claims description 3
- 229950003747 detirelix Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 108010083551 iturelix Proteins 0.000 claims description 2
- QRYFGTULTGLGHU-NBERXCRTSA-N iturelix Chemical compound C([C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CCCCNC(=O)C=1C=NC=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)CCCNC(=O)C1=CC=CN=C1 QRYFGTULTGLGHU-NBERXCRTSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 229950011372 teverelix Drugs 0.000 claims description 2
- SBNPWPIBESPSIF-MHWMIDJBSA-N cetrorelix Chemical compound C([C@@H](C(=O)N[C@H](CCCNC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 SBNPWPIBESPSIF-MHWMIDJBSA-N 0.000 claims 2
- OFQNFLLLCMQNEP-KQCGYNJJSA-N chembl2106408 Chemical compound C([C@@H](C(=O)N[C@@H](CCCCNC(/NCC)=N\CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 OFQNFLLLCMQNEP-KQCGYNJJSA-N 0.000 claims 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- UCANQOXFIYWYIX-IDEADWEOSA-N (2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-(carbamoylamino)pentanoyl]amino]-4-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide 4-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid Chemical compound OC(=O)c1cc2ccccc2c(Cc2c(O)c(cc3ccccc23)C(O)=O)c1O.CC(C)C[C@H](NC(=O)[C@@H](CCCNC(N)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@@H](Cc1cccnc1)NC(=O)[C@@H](Cc1ccc(Cl)cc1)NC(=O)[C@@H](Cc1ccc2ccccc2c1)NC(C)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O.CC(C)C[C@H](NC(=O)[C@@H](CCCNC(N)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@@H](Cc1cccnc1)NC(=O)[C@@H](Cc1ccc(Cl)cc1)NC(=O)[C@@H](Cc1ccc2ccccc2c1)NC(C)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O UCANQOXFIYWYIX-IDEADWEOSA-N 0.000 abstract description 8
- 239000005557 antagonist Substances 0.000 abstract description 2
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 abstract 1
- 102100024028 Progonadoliberin-1 Human genes 0.000 abstract 1
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 abstract 1
- 239000000556 agonist Substances 0.000 abstract 1
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- KFEFLCOCAHJBEA-ANRVCLKPSA-N cetrorelix acetate Chemical compound CC(O)=O.C([C@@H](C(=O)N[C@H](CCCNC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 KFEFLCOCAHJBEA-ANRVCLKPSA-N 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
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- 230000035484 reaction time Effects 0.000 description 3
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- 201000004458 Myoma Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920002253 Tannate Polymers 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940127233 azaline B Drugs 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229960001865 cetrorelix acetate Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- OFQNFLLLCMQNEP-MIPXGPCFSA-N deterelix Chemical compound C([C@@H](C(=O)N[C@H](CCCCN=C(NCC)NCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 OFQNFLLLCMQNEP-MIPXGPCFSA-N 0.000 description 1
- RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 229950005627 embonate Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- 229940121381 gonadotrophin releasing hormone (gnrh) antagonists Drugs 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
- A61P5/04—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin for decreasing, blocking or antagonising the activity of the hypothalamic hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Endocrinology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10040700A DE10040700A1 (de) | 2000-08-17 | 2000-08-17 | Salze von biologisch aktiven Peptiden, ihre Herstellung und Verwendung |
| PCT/EP2001/009219 WO2002014347A2 (de) | 2000-08-17 | 2001-08-09 | Verfahren zur herstellung von peptidsalzen, deren verwendung und die peptidsalze enthaltende pharmazeutische zubereitungen |
| CA002355573A CA2355573A1 (en) | 2000-08-17 | 2001-08-22 | Method for the synthesis of peptide salts, their use and the pharmaceutical preparations, containing peptide salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK3032003A3 true SK3032003A3 (en) | 2004-05-04 |
Family
ID=27805895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK303-2003A SK3032003A3 (en) | 2000-08-17 | 2001-08-09 | Method for producing peptide salts, their use and pharmaceutical preparations containing these peptide salts |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6780972B2 (de) |
| EP (1) | EP1309607B1 (de) |
| JP (1) | JP2004506647A (de) |
| CN (1) | CN1187369C (de) |
| AR (1) | AR030371A1 (de) |
| AT (1) | ATE280779T1 (de) |
| AU (2) | AU1043902A (de) |
| BG (1) | BG107612A (de) |
| BR (1) | BR0113296A (de) |
| CA (1) | CA2355573A1 (de) |
| CZ (1) | CZ2003688A3 (de) |
| DE (2) | DE10040700A1 (de) |
| DK (1) | DK1309607T3 (de) |
| EE (1) | EE200300065A (de) |
| ES (1) | ES2230371T3 (de) |
| HK (1) | HK1058366A1 (de) |
| HU (1) | HUP0300738A3 (de) |
| IL (1) | IL154150A0 (de) |
| MX (1) | MXPA03001448A (de) |
| NO (1) | NO20030618L (de) |
| NZ (1) | NZ524023A (de) |
| PL (1) | PL204496B1 (de) |
| PT (1) | PT1309607E (de) |
| RU (1) | RU2266296C2 (de) |
| SI (1) | SI1309607T1 (de) |
| SK (1) | SK3032003A3 (de) |
| TW (1) | TWI236910B (de) |
| UA (1) | UA74005C2 (de) |
| WO (1) | WO2002014347A2 (de) |
| ZA (1) | ZA200300777B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6828415B2 (en) * | 1993-02-19 | 2004-12-07 | Zentaris Gmbh | Oligopeptide lyophilisate, their preparation and use |
| US7098305B2 (en) * | 2001-09-06 | 2006-08-29 | Ardana Bioscience Limited | Sustained release of microcrystalline peptide suspensions |
| EP1674082A1 (de) * | 2004-12-22 | 2006-06-28 | Zentaris GmbH | Verfahren zur Herstellung von sterilen Suspensionen oder Lyophilisaten schwerlöslicher basischer Peptidkomplexe, diese enthaltende pharmazeutische Formulierungen sowie ihre Verwendung als Arzneimittel |
| RU2525661C2 (ru) * | 2012-11-15 | 2014-08-20 | Федеральное государственное бюджетное учреждение "Научно-исследовательский институт вакцин и сывороток им. И.И. Мечникова" Российской академии медицинских наук (ФГБУ "НИИВС им. И.И. Мечникова" РАМН) | Способ получения высокотитражной антимикробной сыворотки для оценки антигенной активности противостафилококковых вакцин |
| CN107056894B (zh) * | 2017-05-26 | 2021-07-20 | 济南康和医药科技有限公司 | 一种片段法固相合成醋酸加尼瑞克的方法 |
| EP3590526A1 (de) * | 2018-07-05 | 2020-01-08 | Antev Limited | Lyophilisierungsverfahren und dadurch hergestelltes teverelix-tfa-lyophilisat |
| CN114249800A (zh) * | 2020-09-22 | 2022-03-29 | 深圳市星银医药有限公司 | 一种双羟萘酸多肽药物的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4431635A (en) * | 1979-06-13 | 1984-02-14 | Coy David Howard | LH-RH Antagonists |
| EP0041286B1 (de) * | 1980-06-02 | 1984-08-15 | Andrew Victor Schally | LH-RH Antagonisten |
| US4800191A (en) * | 1987-07-17 | 1989-01-24 | Schally Andrew Victor | LHRH antagonists |
| DE4305225A1 (de) * | 1993-02-19 | 1994-08-25 | Asta Medica Ag | Neues Herstellverfahren für Cetrorelix Lyophilisat |
| CA2123144A1 (en) * | 1993-05-10 | 1994-11-11 | David Bodmer | Stabilisation of pharmacologically active compounds in sustained release compositions |
| CA2178592C (en) * | 1993-12-09 | 2009-07-28 | Jurgen Engel | Long-acting injection suspensions and a process for their preparation |
| DE4342092B4 (de) * | 1993-12-09 | 2007-01-11 | Zentaris Gmbh | Langwirkende Injektionssuspension und Verfahren zur Herstellung |
| US6054432A (en) * | 1996-09-12 | 2000-04-25 | Asta Medica Aktiengesellschaft | Means for treating prostate hypertrophy and prostate cancer |
| HUP0100221A3 (en) * | 1998-01-16 | 2002-11-28 | Takeda Pharmaceutical | Sustained release compositions, process for producing the same and utilization thereof |
-
2000
- 2000-08-17 DE DE10040700A patent/DE10040700A1/de not_active Withdrawn
-
2001
- 2001-08-09 EE EEP200300065A patent/EE200300065A/xx unknown
- 2001-08-09 CZ CZ2003688A patent/CZ2003688A3/cs unknown
- 2001-08-09 BR BR0113296-2A patent/BR0113296A/pt not_active IP Right Cessation
- 2001-08-09 SK SK303-2003A patent/SK3032003A3/sk not_active Application Discontinuation
- 2001-08-09 SI SI200130237T patent/SI1309607T1/xx unknown
- 2001-08-09 CN CNB018142192A patent/CN1187369C/zh not_active Expired - Fee Related
- 2001-08-09 AU AU1043902A patent/AU1043902A/xx active Pending
- 2001-08-09 WO PCT/EP2001/009219 patent/WO2002014347A2/de active IP Right Grant
- 2001-08-09 IL IL15415001A patent/IL154150A0/xx not_active IP Right Cessation
- 2001-08-09 NZ NZ524023A patent/NZ524023A/en unknown
- 2001-08-09 RU RU2003107560/04A patent/RU2266296C2/ru not_active IP Right Cessation
- 2001-08-09 DE DE50104316T patent/DE50104316D1/de not_active Expired - Lifetime
- 2001-08-09 PT PT01978273T patent/PT1309607E/pt unknown
- 2001-08-09 PL PL359495A patent/PL204496B1/pl not_active IP Right Cessation
- 2001-08-09 DK DK01978273T patent/DK1309607T3/da active
- 2001-08-09 AT AT01978273T patent/ATE280779T1/de not_active IP Right Cessation
- 2001-08-09 MX MXPA03001448A patent/MXPA03001448A/es active IP Right Grant
- 2001-08-09 JP JP2002519484A patent/JP2004506647A/ja active Pending
- 2001-08-09 HU HU0300738A patent/HUP0300738A3/hu unknown
- 2001-08-09 ES ES01978273T patent/ES2230371T3/es not_active Expired - Lifetime
- 2001-08-09 AU AU2002210439A patent/AU2002210439B2/en not_active Ceased
- 2001-08-09 EP EP01978273A patent/EP1309607B1/de not_active Expired - Lifetime
- 2001-08-16 AR ARP010103935A patent/AR030371A1/es active IP Right Grant
- 2001-08-17 TW TW090120293A patent/TWI236910B/zh active
- 2001-08-22 CA CA002355573A patent/CA2355573A1/en not_active Abandoned
- 2001-08-24 US US09/939,532 patent/US6780972B2/en not_active Expired - Fee Related
- 2001-09-08 UA UA2003032260A patent/UA74005C2/uk unknown
-
2003
- 2003-01-29 ZA ZA200300777A patent/ZA200300777B/xx unknown
- 2003-02-07 NO NO20030618A patent/NO20030618L/no unknown
- 2003-03-06 BG BG107612A patent/BG107612A/bg unknown
-
2004
- 2004-02-13 HK HK04101030A patent/HK1058366A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC9A | Refused patent application |